black slim fit dress shirt goTIELESS Ultimate (Black) A solid hue lends versatility to a good Taormina Button-Down Shirt — Black

Under $250 If your budget allows spending between $100 and $250, here are some options to choose from Beckett Simonon In the same vein as Toms or Warby Parker, Beckett Simonon is focused on sourcing responsibly, supporting ethical manufacturing, and acting sustainably

100% Rayon, Bust lining 100% Rayon, imported

Versatile and statement-ready, it transitions effortlessly from daytime events to evening moments

However, it is all about details, particularly your choice of shoes

TIP: One of the chicest ways to dress up a winter maxi dress is to wear it with a structured overcoat (think double breasted navy or camel) or a trench coat and knee high boots